diff --git a/tsdb/engine/tsm1/compact.go b/tsdb/engine/tsm1/compact.go
index c4be1156766..6da71e136cf 100644
--- a/tsdb/engine/tsm1/compact.go
+++ b/tsdb/engine/tsm1/compact.go
@@ -17,6 +17,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"io/fs"
 	"math"
 	"os"
 	"path/filepath"
@@ -65,6 +66,10 @@ func (e errCompactionInProgress) Error() string {
 	return "compaction in progress"
 }
 
+func (e errCompactionInProgress) Unwrap() error {
+	return e.err
+}
+
 type errCompactionAborted struct {
 	err error
 }
@@ -1051,6 +1056,7 @@ func (c *Compactor) removeTmpFiles(files []string) error {
 func (c *Compactor) writeNewFiles(generation, sequence int, src []string, iter KeyIterator, throttle bool, logger *zap.Logger) ([]string, error) {
 	// These are the new TSM files written
 	var files []string
+	var eInProgress errCompactionInProgress
 
 	for {
 		sequence++
@@ -1060,15 +1066,15 @@ func (c *Compactor) writeNewFiles(generation, sequence int, src []string, iter K
 		logger.Debug("Compacting files", zap.Int("file_count", len(src)), zap.String("output_file", fileName))
 
 		// Write as much as possible to this file
-		err := c.write(fileName, iter, throttle, logger)
+		rollToNext, err := c.write(fileName, iter, throttle, logger)
 
-		// We've hit the max file limit and there is more to write.  Create a new file
-		// and continue.
-		if err == errMaxFileExceeded || err == ErrMaxBlocksExceeded {
+		if rollToNext {
+			// We've hit the max file limit and there is more to write.  Create a new file
+			// and continue.
 			files = append(files, fileName)
 			logger.Debug("file size or block count exceeded, opening another output file", zap.String("output_file", fileName))
 			continue
-		} else if err == ErrNoValues {
+		} else if errors.Is(err, ErrNoValues) {
 			logger.Debug("Dropping empty file", zap.String("output_file", fileName))
 			// If the file only contained tombstoned entries, then it would be a 0 length
 			// file that we can drop.
@@ -1076,9 +1082,14 @@ func (c *Compactor) writeNewFiles(generation, sequence int, src []string, iter K
 				return nil, err
 			}
 			break
-		} else if _, ok := err.(errCompactionInProgress); ok {
-			// Don't clean up the file as another compaction is using it.  This should not happen as the
-			// planner keeps track of which files are assigned to compaction plans now.
+		} else if errors.As(err, &eInProgress) {
+			if !errors.Is(eInProgress.err, fs.ErrExist) {
+				logger.Error("error creating compaction file", zap.String("output_file", fileName), zap.Error(err))
+			} else {
+				// Don't clean up the file as another compaction is using it.  This should not happen as the
+				// planner keeps track of which files are assigned to compaction plans now.
+				logger.Warn("file exists, compaction in progress already", zap.String("output_file", fileName))
+			}
 			return nil, err
 		} else if err != nil {
 			// We hit an error and didn't finish the compaction.  Abort.
@@ -1100,10 +1111,10 @@ func (c *Compactor) writeNewFiles(generation, sequence int, src []string, iter K
 	return files, nil
 }
 
-func (c *Compactor) write(path string, iter KeyIterator, throttle bool, logger *zap.Logger) (err error) {
+func (c *Compactor) write(path string, iter KeyIterator, throttle bool, logger *zap.Logger) (rollToNext bool, err error) {
 	fd, err := os.OpenFile(path, os.O_CREATE|os.O_RDWR|os.O_EXCL, 0666)
 	if err != nil {
-		return errCompactionInProgress{err: err}
+		return false, errCompactionInProgress{err: err}
 	}
 
 	// syncingWriter ensures that whatever we wrap the above file descriptor in
@@ -1128,33 +1139,31 @@ func (c *Compactor) write(path string, iter KeyIterator, throttle bool, logger *
 	// in memory.
 	if iter.EstimatedIndexSize() > 64*1024*1024 {
 		w, err = NewTSMWriterWithDiskBuffer(limitWriter)
-		if err != nil {
-			return err
-		}
 	} else {
 		w, err = NewTSMWriter(limitWriter)
-		if err != nil {
-			return err
-		}
 	}
-
+	if err != nil {
+		// Close the file and return if we can't create the TSMWriter
+		return false, errors.Join(err, fd.Close())
+	}
 	defer func() {
+		var eInProgress errCompactionInProgress
+
+		errs := make([]error, 0, 3)
+		errs = append(errs, err)
 		closeErr := w.Close()
-		if err == nil {
-			err = closeErr
-		}
+		errs = append(errs, closeErr)
 
-		// Check for errors where we should not remove the file
-		_, inProgress := err.(errCompactionInProgress)
-		maxBlocks := err == ErrMaxBlocksExceeded
-		maxFileSize := err == errMaxFileExceeded
-		if inProgress || maxBlocks || maxFileSize {
+		// Check for conditions where we should not remove the file
+		inProgress := errors.As(err, &eInProgress) && errors.Is(eInProgress.err, fs.ErrExist)
+		if (closeErr == nil) && (inProgress || rollToNext) {
+			// do not join errors, there is only the one.
 			return
+		} else if err != nil || closeErr != nil {
+			// Remove the file, we have had a problem
+			errs = append(errs, w.Remove())
 		}
-
-		if err != nil {
-			_ = w.Remove()
-		}
+		err = errors.Join(errs...)
 	}()
 
 	lastLogSize := w.Size()
@@ -1164,38 +1173,38 @@ func (c *Compactor) write(path string, iter KeyIterator, throttle bool, logger *
 		c.mu.RUnlock()
 
 		if !enabled {
-			return errCompactionAborted{}
+			return false, errCompactionAborted{}
 		}
 		// Each call to read returns the next sorted key (or the prior one if there are
 		// more values to write).  The size of values will be less than or equal to our
 		// chunk size (1000)
 		key, minTime, maxTime, block, err := iter.Read()
 		if err != nil {
-			return err
+			return false, err
 		}
 
 		if minTime > maxTime {
-			return fmt.Errorf("invalid index entry for block. min=%d, max=%d", minTime, maxTime)
+			return false, fmt.Errorf("invalid index entry for block. min=%d, max=%d", minTime, maxTime)
 		}
 
 		// Write the key and value
-		if err := w.WriteBlock(key, minTime, maxTime, block); err == ErrMaxBlocksExceeded {
+		if err := w.WriteBlock(key, minTime, maxTime, block); errors.Is(err, ErrMaxBlocksExceeded) {
 			if err := w.WriteIndex(); err != nil {
-				return err
+				return false, err
 			}
-			return err
+			return true, err
 		} else if err != nil {
-			return err
+			return false, err
 		}
 
-		// If we have a max file size configured and we're over it, close out the file
+		// If we're over maxTSMFileSize, close out the file
 		// and return the error.
 		if w.Size() > maxTSMFileSize {
 			if err := w.WriteIndex(); err != nil {
-				return err
+				return false, err
 			}
 
-			return errMaxFileExceeded
+			return true, errMaxFileExceeded
 		} else if (w.Size() - lastLogSize) > logEvery {
 			logger.Debug("Compaction progress", zap.String("output_file", path), zap.Uint32("size", w.Size()))
 			lastLogSize = w.Size()
@@ -1204,15 +1213,15 @@ func (c *Compactor) write(path string, iter KeyIterator, throttle bool, logger *
 
 	// Were there any errors encountered during iteration?
 	if err := iter.Err(); err != nil {
-		return err
+		return false, err
 	}
 
 	// We're all done.  Close out the file.
 	if err := w.WriteIndex(); err != nil {
-		return err
+		return false, err
 	}
 	logger.Debug("Compaction finished", zap.String("output_file", path), zap.Uint32("size", w.Size()))
-	return nil
+	return false, nil
 }
 
 func (c *Compactor) add(files []string) bool {
diff --git a/tsdb/engine/tsm1/compact_test.go b/tsdb/engine/tsm1/compact_test.go
index c90beb6b1cf..ccfa6d4f469 100644
--- a/tsdb/engine/tsm1/compact_test.go
+++ b/tsdb/engine/tsm1/compact_test.go
@@ -1,7 +1,9 @@
 package tsm1_test
 
 import (
+	"errors"
 	"fmt"
+	"io/fs"
 	"math"
 	"os"
 	"path/filepath"
@@ -12,6 +14,7 @@ import (
 
 	"github.com/influxdata/influxdb/tsdb"
 	"github.com/influxdata/influxdb/tsdb/engine/tsm1"
+	"github.com/stretchr/testify/assert"
 	"go.uber.org/zap"
 )
 
@@ -113,11 +116,11 @@ func TestCompactor_CompactFullLastTimestamp(t *testing.T) {
 	}
 	f2 := MustWriteTSM(dir, 2, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Open()
 
 	files, err := compactor.CompactFull([]string{f1, f2}, zap.NewNop())
@@ -170,11 +173,11 @@ func TestCompactor_CompactFull(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 
 	files, err := compactor.CompactFull([]string{f1, f2, f3}, zap.NewNop())
 	if err == nil {
@@ -280,11 +283,11 @@ func TestCompactor_DecodeError(t *testing.T) {
 	f.WriteAt([]byte("ffff"), 10) // skip over header
 	f.Close()
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 
 	files, err := compactor.CompactFull([]string{f1, f2, f3}, zap.NewNop())
 	if err == nil {
@@ -326,11 +329,11 @@ func TestCompactor_Compact_OverlappingBlocks(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 
 	compactor.Open()
@@ -406,11 +409,11 @@ func TestCompactor_Compact_OverlappingBlocksMultiple(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 
 	compactor.Open()
@@ -620,11 +623,11 @@ func TestCompactor_CompactFull_SkipFullBlocks(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 	compactor.Open()
 
@@ -722,11 +725,11 @@ func TestCompactor_CompactFull_TombstonedSkipBlock(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 	compactor.Open()
 
@@ -825,11 +828,11 @@ func TestCompactor_CompactFull_TombstonedPartialBlock(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 	compactor.Open()
 
@@ -933,11 +936,11 @@ func TestCompactor_CompactFull_TombstonedMultipleRanges(t *testing.T) {
 	}
 	f3 := MustWriteTSM(dir, 3, writes)
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Size = 2
 	compactor.Open()
 
@@ -1049,11 +1052,11 @@ func TestCompactor_CompactFull_MaxKeys(t *testing.T) {
 	}
 	f2.Close()
 
-	fs := &fakeFileStore{}
-	defer fs.Close()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
 	compactor := tsm1.NewCompactor()
 	compactor.Dir = dir
-	compactor.FileStore = fs
+	compactor.FileStore = ffs
 	compactor.Open()
 
 	// Compact both files, should get 2 files back
@@ -1086,6 +1089,61 @@ func TestCompactor_CompactFull_MaxKeys(t *testing.T) {
 	}
 }
 
+func TestCompactor_CompactFull_InProgress(t *testing.T) {
+	// This test creates a lot of data and causes timeout failures for these envs
+	if testing.Short() || os.Getenv("CI") != "" || os.Getenv("GORACE") != "" {
+		t.Skip("Skipping in progress compaction test")
+	}
+	dir := MustTempDir()
+	defer os.RemoveAll(dir)
+
+	f2Name := func() string {
+		values := make([]tsm1.Value, 1000)
+
+		// Write a new file with 2 blocks
+		f2, f2Name := MustTSMWriter(dir, 2)
+		defer func() {
+			assert.NoError(t, f2.Close(), "closing TSM file %s", f2Name)
+		}()
+		for i := 0; i < 2; i++ {
+			values = values[:0]
+			for j := 0; j < 1000; j++ {
+				values = append(values, tsm1.NewValue(int64(i*1000+j), int64(1)))
+			}
+			assert.NoError(t, f2.Write([]byte("cpu,host=A#!~#value"), values), "writing TSM file: %s", f2Name)
+		}
+		assert.NoError(t, f2.WriteIndex(), "writing TSM file index for %s", f2Name)
+		return f2Name
+	}()
+	ffs := &fakeFileStore{}
+	defer ffs.Close()
+	compactor := tsm1.NewCompactor()
+	compactor.Dir = dir
+	compactor.FileStore = ffs
+	compactor.Open()
+
+	expGen, expSeq, err := tsm1.DefaultParseFileName(f2Name)
+	assert.NoError(t, err, "unexpected error parsing file name %s", f2Name)
+	expSeq = expSeq + 1
+
+	fileName := filepath.Join(compactor.Dir, tsm1.DefaultFormatFileName(expGen, expSeq)+"."+tsm1.TSMFileExtension+"."+tsm1.TmpTSMFileExtension)
+
+	// Create a temp file to simulate an in progress compaction
+	f, err := os.Create(fileName)
+	assert.NoError(t, err, "creating in-progress compaction file %s", fileName)
+	defer func() {
+		assert.NoError(t, f.Close(), "closing in-progress compaction file %s", fileName)
+	}()
+	_, err = compactor.CompactFull([]string{f2Name}, zap.NewNop())
+	assert.Errorf(t, err, "expected an error writing snapshot for %s", f2Name)
+	e := errors.Unwrap(err)
+	assert.NotNil(t, e, "expected an error wrapped by errCompactionInProgress")
+	assert.Truef(t, errors.Is(e, fs.ErrExist), "error did not indicate file existence: %v", e)
+	pathErr := &os.PathError{}
+	assert.Truef(t, errors.As(e, &pathErr), "expected path error, got %v", e)
+	assert.Truef(t, errors.Is(pathErr, fs.ErrExist), "error did not indicate file existence: %v", pathErr)
+}
+
 func newTSMKeyIterator(size int, fast bool, interrupt chan struct{}, readers ...*tsm1.TSMReader) (tsm1.KeyIterator, error) {
 	files := []string{}
 	for _, r := range readers {
@@ -2529,14 +2587,14 @@ func TestDefaultPlanner_Plan_SkipPlanningAfterFull(t *testing.T) {
 		},
 	}
 
-	fs := &fakeFileStore{
+	ffs := &fakeFileStore{
 		PathsFn: func() []tsm1.FileStat {
 			return testSet
 		},
 		blockCount: 1000,
 	}
 
-	cp := tsm1.NewDefaultPlanner(fs, time.Nanosecond)
+	cp := tsm1.NewDefaultPlanner(ffs, time.Nanosecond)
 	plan, pLen := cp.Plan(time.Now().Add(-time.Second))
 	// first verify that our test set would return files
 	if exp, got := 4, len(plan[0]); got != exp {
@@ -2595,9 +2653,9 @@ func TestDefaultPlanner_Plan_SkipPlanningAfterFull(t *testing.T) {
 	}
 	cp.Release(plan)
 
-	cp.FileStore = fs
+	cp.FileStore = ffs
 	// ensure that it will plan if last modified has changed
-	fs.lastModified = time.Now()
+	ffs.lastModified = time.Now()
 
 	cGroups, pLen := cp.Plan(time.Now())
 	if exp, got := 4, len(cGroups[0]); got != exp {
@@ -2693,7 +2751,7 @@ func TestDefaultPlanner_Plan_NotFullOverMaxsize(t *testing.T) {
 		},
 	}
 
-	fs := &fakeFileStore{
+	ffs := &fakeFileStore{
 		PathsFn: func() []tsm1.FileStat {
 			return testSet
 		},
@@ -2701,7 +2759,7 @@ func TestDefaultPlanner_Plan_NotFullOverMaxsize(t *testing.T) {
 	}
 
 	cp := tsm1.NewDefaultPlanner(
-		fs,
+		ffs,
 		time.Nanosecond,
 	)
 
diff --git a/tsdb/engine/tsm1/writer.go b/tsdb/engine/tsm1/writer.go
index 4784dc6d558..70f0fd77e22 100644
--- a/tsdb/engine/tsm1/writer.go
+++ b/tsdb/engine/tsm1/writer.go
@@ -66,6 +66,7 @@ import (
 	"bufio"
 	"bytes"
 	"encoding/binary"
+	"errors"
 	"fmt"
 	"hash/crc32"
 	"io"
@@ -511,19 +512,15 @@ func (d *directIndex) Size() uint32 {
 }
 
 func (d *directIndex) Close() error {
+	errs := make([]error, 0, 3)
 	// Flush anything remaining in the index
-	if err := d.w.Flush(); err != nil {
-		return err
-	}
-
-	if d.fd == nil {
-		return nil
+	errs = append(errs, d.w.Flush())
+	if d.fd != nil {
+		// Close and remove the temporary index file
+		errs = append(errs, d.fd.Close())
+		errs = append(errs, os.Remove(d.fd.Name()))
 	}
-
-	if err := d.fd.Close(); err != nil {
-		return err
-	}
-	return os.Remove(d.fd.Name())
+	return errors.Join(errs...)
 }
 
 // Remove removes the index from any tempory storage
@@ -532,11 +529,14 @@ func (d *directIndex) Remove() error {
 		return nil
 	}
 
-	// Close the file handle to prevent leaking.  We ignore the error because
-	// we just want to cleanup and remove the file.
-	_ = d.fd.Close()
-
-	return os.Remove(d.fd.Name())
+	errs := make([]error, 0, 2)
+	// Close the file handle to prevent leaking.
+	// We don't let an error stop the removal.
+	if err := d.fd.Close(); err != nil && !errors.Is(err, os.ErrClosed) {
+		errs = append(errs, err)
+	}
+	errs = append(errs, os.Remove(d.fd.Name()))
+	return errors.Join(errs...)
 }
 
 // tsmWriter writes keys and values in the TSM format
@@ -756,25 +756,19 @@ func (t *tsmWriter) sync() error {
 }
 
 func (t *tsmWriter) Close() error {
-	if err := t.Flush(); err != nil {
-		return err
-	}
-
-	if err := t.index.Close(); err != nil {
-		return err
-	}
-
+	errs := make([]error, 0, 3)
+	errs = append(errs, t.Flush())
+	errs = append(errs, t.index.Close())
 	if c, ok := t.wrapped.(io.Closer); ok {
-		return c.Close()
+		errs = append(errs, c.Close())
 	}
-	return nil
+	return errors.Join(errs...)
 }
 
 // Remove removes any temporary storage used by the writer.
 func (t *tsmWriter) Remove() error {
-	if err := t.index.Remove(); err != nil {
-		return err
-	}
+	errs := make([]error, 0, 3)
+	errs = append(errs, t.index.Remove())
 
 	// nameCloser is the most permissive interface we can close the wrapped
 	// value with.
@@ -783,14 +777,16 @@ func (t *tsmWriter) Remove() error {
 		Name() string
 	}
 
+	// If the writer is not a memory buffer, we can remove the file.
 	if f, ok := t.wrapped.(nameCloser); ok {
-		// Close the file handle to prevent leaking.  We ignore the error because
-		// we just want to cleanup and remove the file.
-		_ = f.Close()
-
-		return os.Remove(f.Name())
+		// Close the file handle to prevent leaking.
+		if err := f.Close(); err != nil && !errors.Is(err, os.ErrClosed) {
+			errs = append(errs, err)
+		}
+		// Remove the file
+		errs = append(errs, os.Remove(f.Name()))
 	}
-	return nil
+	return errors.Join(errs...)
 }
 
 func (t *tsmWriter) Size() uint32 {